r/digitalnomad

I’m on my 5th country now and it’s really really draining me to say the least trying to eat healthily and not spend huge amounts of money. I tend to stay in places for at least a month at a time.

Ordering groceries online is a pain and they only have limited stock.

Big supermarkets are far away and require taxing to and from with all groceries.

The convenience store food is all processed and full of sodium and I don’t want to eat it x3 a day

Some places is hard to rent with a kitchen or it’s so expensive.

Trying to maintain a somewhat healthy lifestyle with gym and high protein and it’s just annoying the hell out of me.

I've been working remotely for about two years now and recently started moving more frequently, sometimes every two to three weeks. At first it felt like the dream: new city, new energy, new inspiration. But lately I'm noticing a real tension between constant movement and actually getting deep work done.

The onboarding phase of a new place eats into productive hours more than I expected. Finding decent wifi, figuring out time zones for client calls, adjusting sleep, scouting a good cafe or coworking space. It all adds up. The social side is exhausting too. You meet great people, build a little routine, and then you're gone.

I'm curious how others here have navigated this. Did you eventually settle on a slower pace, like one to three months per location? Or did you find systems that make fast movement sustainable long term?

Also wondering if the type of work matters a lot. Someone doing async writing or design probably has a pretty different experience than someone managing live client calls across multiple time zones.

Not looking for the romanticized version. More interested in the honest day to day reality people have landed on after a year or two of doing this seriously. What actually worked for you, and what did you have to give up to make it work?

I've been putting off upgrading my headphones because every review seems to recommend something different.

I mainly care about:

• Sound quality for music
• Comfort during long work sessions
• Noise cancellation for cafés, airports, and flights
• Battery life
• Durability over time

I'm not looking for the "objectively best" pair—I'm more interested in what has actually held up in real life.

What headphones are you using, how long have you had them, and would you buy them again?

If you switched from another pair, what made you change? And if you've tried multiple brands (Sony, Bose, Apple, Sennheiser, Audio-Technica, etc.), which one ended up being your favorite and why?

I'd love to hear both the headphones you swear by and the ones you'd never buy again.

Something I've been thinking about a lot lately and don't see discussed enough here. Everyone talks about the freedom, the locations, the cost of living hacks. But what about the slow erosion of close friendships over time?

I've been working remotely and moving around for about two years now. At first the people back home were excited, asking questions, following along. But gradually the calls get shorter, the checkins less frequent, and you start to realize you're living in completely different rhythms. It gets hard to relate to each other anymore.

Then there's the friendships you make on the road. Genuinely great people, real connections, but everyone moves on within weeks or months. You end up with this wide but shallow social network spread across a dozen time zones.

I'm not complaining exactly, more just processing it out loud. I've read a lot about the logistical side of this lifestyle but the social and emotional toll feels like the thing nobody actually prepares you for.

Curious how others have handled this. Have you found ways to maintain deep friendships long distance? Do you intentionally slow down your travel pace to build more roots somewhere? Or have you just accepted a different kind of social life as part of the deal?

I'm planning to spend 6 months in Latin America. I will spend 3 in Peru, 1 in Argentina, and 1 in Mexico. I'm trying to decide where to spend the fourth one as there isn't really anywhere else I want to go to besides Puerto Rico and potentially Brazil, but I think it's a bit too expensive for me. I've already been to Guatemala.

I speak fluent Spanish but only A2 to B1 Portuguese. I would be able to get by, but it would be difficult to do much more than that. I have about 8 months to practice, but I only have an hour of time per day that I can set aside to practice.

Being able to speak the local language decently well at minimum is very important to me because I want to be able to meet people who are from the country without worrying about if they speak English. I don't want to have to rely on people speaking English and I don't want to hang out around only foreigners.

Is Brazil good enough to spend the next 8 months working on Portuguese? Or should I just stick to Spanish-speaking countries? If I were to go to Brazil, what city would be a good place to spend 1 month in?

Hi all,

I'm currently considering leaving the Netherlands officially, since I'm mostly living in Indonesia. I'm a IT freelancer, having clients in Australia, currently getting paid via my Dutch company. I'm now registered as a freelancer (ZZP) and paying my tax in the Netherlands while not being located there anymore. So I'm considering starting an LLC, while paying my taxes in Indonesia. Does anyone know an international tax advisor who can help me with this? It would be even better if that person knows Dutch tax as well. Maybe some Dutch people who did the same?

Very much appreciated!

title, basically. idk fun question.

I'm researching how people legally work remotely in Japan for companies without a Japanese entity.

I keep seeing companies use an Employer of Record Japan service to handle international employment, global payroll, tax compliance, and workforce management.

For those actually using an EOR, are you considered a normal employee under the EOR?

Do they take care of your Japan income tax, pension, health insurance, and other social insurance Japan requirements?

Or are you still responsible for everything like a contractor?

Trying to understand the difference between an EOR employee setup vs an independent contractor agreement, especially around visas, taxes, and compliance.

How do you afford the cost of living when you have an inconsistent work doing remote work? If you can ever even find a remote work.

I'm from India and will be traveling around nearby countries for the next couple of months. I started betting during the World Cup and have been using crypto for deposits/withdrawals. Not sure how it works with melbet when you move between countries. Will I have any problems, or does it work fine while traveling?

Curious about this situation and if anyone else is making this work

I will be out of the county most of the year and currently live in income tax free state of Washington, this is the address I currently have listed at work (this home will be sold shortly so I think I will have to change the address with my work at some point)

I plan to get one of those domiciled addresses in Florida for mail/taxes and FL ID eventually

The problem is I only have family in California I can leave V--P--N with. So technically my work would see me constantly logging in with a Cali IP but my actual address with them is a whole other state

What are others doing in this situation? I'm not trying to evade taxes and plan to file them but I also don't want to get stuck having to file them for California where I will not be living at any point(they are the highest tax state 😩)

I made the switch to working remotely from another country and the actual work part was the easy piece. Nobody warned me about the banking situation.

Your US bank sees sustained foreign transactions and starts asking questions. Some accounts get flagged. Some get closed with almost no notice. Meanwhile you're trying to pay rent in a country where cash is still king in most places and your Venmo is useless.

What actually saved me was setting up the financial infrastructure before I left — not after I needed it. Schwab checking for the ATM situation, Wise for receiving payments in different currencies, kept one US address active for anything that needed it. Took maybe two weeks to sort out before the move and saved me from what I watched other people go through their first few months.

Curious what others did — especially people who freelance or have clients in multiple countries. How did you handle getting paid once you were no longer in the US?

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For context, i am both Chilean and Canadian citizen.

I worked 6 years remotely for a company in Canada. My company is fully remote and I pay taxes there (T4, they automatically deduct it), but I've been living in Chile for a year (so definitely more than 183 days) and plan to stay a couple more years for family reasons, and I'm still with the same canadian company.

It seems there is a treaty between Chile and Canada that prevents double taxation, but it's not automatic, and sometimes it may not even apply, and I could end up having to pay double.

Has anyone been in a similar situation? I just want to be at ease without worrying that years down the line the SII (or CRA) might come after me for millions.

The 3 year Chilean rule doesnt apply to me as I already lived until my 30s in Chile.

I'm also grateful for any info on accountants who specialize in international taxes.

what cities do you feel make life easiest for a digital nomad, the places where you have felt most comfortable and where every day life was more practical for a foreign visitor doing a multi month stay?

On a related note, are there any places where you just couldn’t adapt, either because things were too chaotic, disorganized or for another reason, and which you would avoid during your future travels?

I hear horror stories about some nomads getting detained or arrested when customs or police discover a person has adderall or Xanax on them. Even in the prescription bottle.

These stories never really say how much they had on them though or if they followed those countries protocols of declaring it beforehand.

Any of you had any issues traveling with similar prescriptions?

I’m in Japan for a one-month business trip and would like to stay after the project ends. My cost of living is around $2000/month, covering rent, food, and bills. I lived in Thailand for three years and travelled from there for work, so this lifestyle isn’t new to me. I hold Brazilian and Italian passports.

How do people rent a place in Japan for longer than a month? Do you sign a formal contract, or is it mostly done online? Any guidance on renting and keeping costs near $2000/month would be appreciated.

Edit: I’m fine with not furnished apartment

I’m middle aged and have worked in nonprofits (libraries, museums, universities) for most of my career. My masters degree is in library and information science and I am looking to pivot skills into digital nomad type work language.

I have project management, data management, records and archives management, grant management, program management, database management (but not backend).

I can write/communicate effectively, I like people and can I’m good at instruction and explaining or detailing processes. I’m also a researcher and have some background in photography and film, as well as music and art.

I know a little about a lot but I’m liberal arts and humanities centered. Cultural theory, philosophy, literature etc…

Are there skills that I possess that translate into digital nomad job frameworks?

I’d love to know if this sparks any ideas. My contract is ending and I’d love a new adventure. No kids. No pets.

Thanks for any and all ideas!

I'm talking about exiting the country then re-entering it again for a significant length of time over and over with ease.

I remember doing this in Thailand back in 2019, but have been told it's been patched - is this true?

Alternatively,

In places like the Philippines, they just explicitly allow you to abuse the tourist visa no questions asked - you just go to the Bureau of Immigration, pay a fee and extend your visa.

You can do this for upto three years without any issue.

When you max out your three years, you can fly out of the country for at least 24 hours, fly back and reset the three year timer again.

So... where else is like this? Either where you can visa run endlessly or just get stupidly long visas/visa extensions without any real requirements?

LLM tools are not very good at telling you the ground reality, hence why I'm asking here.

British citizen for reference.

For more context I have been living in a new place for a bit and realized I have basically no idea what's actually happening around me unless it's big enough to hit international news. Like local political stuff, strikes, protests, even just weird local events that would be useful to know about, I just don't see any of it until a friend mentions it or I stumble on it randomly.

Google News is mostly just global headlines and stuff about my home country. Following local news sites is rough when it's not in english or paywalled. And expat Facebook groups are hit or miss, sometimes useful sometimes just people complaining about visas.

How do you guys actually stay in the loop when you move somewhere new? Do you follow specific accounts, join local telegram groups, just ask locals, or is everyone just kind of flying blind like me.